Hydrogen peroxide is a clean and excellent oxidizing agent which is inexpensive, and easily handled, and becomes harmless water after reaction, and an oxidation reaction using hydrogen peroxide as an oxidizing agent has been highlighted as one of environmentally friendly production processes. In development of an oxidation reaction using hydrogen peroxide as an oxidizing agent, it is important to develop a catalyst for the oxidation reaction. In particular, from the industrial viewpoint, it has been desired to develop a solid catalyst which is advantageous to separation and recovery of a catalyst from a reaction system. For example, regarding a titanium-containing mesoporous silicate which is one of solid catalysts, industrial utilization as an epoxidation catalyst of olefin compounds and as a catalyst for ammoximation of ketone compounds has been studied.
On the other hand, a solid catalyst containing a metal other than titanium and having different catalytic performance and catalytic activity from a titanium-containing mesoporous silicate has also been developed. For example, regarding a tungsten-containing mesoporous silicate, as a catalyst for producing cyclohexanediol by reacting cyclohexene and hydrogen peroxide, Applied Catalysis A, 179, 11 (1999), and Chem. Commun., 241 (1998) report a tungsten-containing mesoporous silicate produced by reacting a tetraalkoxysilane and ammonium tungstate using cetyl pyridinium bromide as a template in a strongly acidic solvent. However, such a tungsten-containing mesoporous silicate alone has low activity and, in order to obtain sufficient activity, acetic acid should be used as a reaction solvent.
For example, regarding a molybdenum-containing mesoporous silicate, as a catalyst for producing phenol by reacting benzene and hydrogen peroxide, Chem. Commun., 979 (1996) reports a molybdenum-containing mesoporous silicate produced by reacting potassium molybdate and a tetraalkoxysilane in a water-ethanol solvent in the presence of dodecylamine, filtering and washing the reaction product, and calcining the resulting crystals at 923K.
For example, regarding a vanadium-containing mesoporous silicate, as a catalyst for producing a quinone compound by reacting phenol or naphthol and hydrogen peroxide, J. Chem. Soc., Chem. Commun., 2231 (1995), p. 2231, left column, middle paragraph, and J. Chem. Soc., Chem. Commun., 1059 (1994) report a vanadium-containing mesoporous silicate obtained by reacting a solution obtained by adding vanadium sulfate to tetraalkoxysilane in a mixed solution of ethanol and isopropanol, with an aqueous solution containing dodecylamine and hydrochloric acid, filtering and washing the resulting crystals, and calcining them. In addition, from the results of XRD spectrum measurement, these silicate compounds are reported to be all MCM-41 type.
Further, regarding an oxidation reaction using hydrogen peroxide as an oxidizing agent, an oxidation reaction for an olefin compound and a Baeyer-Villiger oxidation reaction for a ketone compound are important, and a method using a solid catalyst has also been proposed. For example, a 2-alkoxyalcohol compound is generally produced by a two-stage method, wherein an olefin compound is once oxidized to convert it into an epoxide compound and then the epoxide compound is reacted with an alcohol compound. U.S. Pat. No. 6,239,315 proposes a one-stage process for producing a 2-alkoxyalcohol compound by reacting an olefin compound, hydrogen peroxide and an alcohol compound using two kinds of solid catalysts having different performances of a titania silicate catalyst having oxidation catalytic capability and a ZSM-5 catalyst having alkylation catalytic capability. However, there was a problem that two kinds of the expensive compounds should be used as the catalysts. As a method without using such two kinds of compounds as catalysts, New. J. Chem., 1998, 797–799 reports a method using a titanium-containing β-type zeolite. However, since a diol is produced as a by-product, selectivity of a 2-alkoxyalcohol is not high and, in order to prevent production of a diol as a by-product, anhydrous hydrogen peroxide should be used, which is problematic from the viewpoint of prevention of disasters.
Furthermore, as a method for obtaining a lactone compound or an ester compound by subjecting a ketone compound to a Baeyer-Villiger oxidation with hydrogen peroxide, for example, Nature, 412, 423 (2001), and Chem. Commun., 2190 (2001) report a method using a zeolite-β catalyst carrying tin, and JP 2001-232205 A reports a method using a silica catalyst carrying antimony fluoride. However, these methods use toxic tin and expensive antimony fluoride, and they can not be necessarily said to be industrial catalysts.
Moreover, as a method for obtaining an aromatic ester compound by using an aromatic aldehyde compound, hydrogen peroxide and an alcohol solvent, for example, a method using TS-1 as a catalyst (SynLett, 267 (2002)) and a method of using vanadium oxide and perchloric acid together (Organic Lett., 2, 577 (2000)) are reported. However, in the former, the reaction yield is low and, in the latter, perchloric acid which requires careful handling should be used together. Therefore, these catalysts can not necessarily be said to be industrial catalysts.